It seems to me to go with the participle λυπούμενον - 'it was irritated, being distressed (better: 'because it was being distressed') on purpose by the maid'; ie ὑπο + gen to express agent with a passive participle.

I'm not sure though if it actually might go with ἐδυσκολαινεν, and, if so, I guess it would have to be translated as 'was irritated because of the maid, being distressed on purpose'.

I know ultimately it doesn't make much difference, but help would be appreciated!

Agreed. ὑπό used of agency with the passive makes it almost impossible here to take it any other way, and clues the reader that λυπούμενον is certainly understood as a passive here. "Because of the maid" would probably be διὰ τὴν θερἀπαιναν...

Agreed. ὑπό used of agency with the passive makes it almost impossible here to take it any other way, and clues the reader that λυπούμενον is certainly understood as a passive here. "Because of the maid" would probably be διὰ τὴν θερἀπαιναν...